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WO2011075871A1 - Autobronzant avec pyrannones et furannones - Google Patents

Autobronzant avec pyrannones et furannones Download PDF

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Publication number
WO2011075871A1
WO2011075871A1 PCT/CN2009/001544 CN2009001544W WO2011075871A1 WO 2011075871 A1 WO2011075871 A1 WO 2011075871A1 CN 2009001544 W CN2009001544 W CN 2009001544W WO 2011075871 A1 WO2011075871 A1 WO 2011075871A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
composition according
adjuvant
sunless tanning
tanning agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2009/001544
Other languages
English (en)
Inventor
Joseph Oreste Carnali
Weimin Peng
Xiaoxia Yang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hindustan Unilever Ltd
Unilever NV
Original Assignee
Hindustan Unilever Ltd
Unilever NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hindustan Unilever Ltd, Unilever NV filed Critical Hindustan Unilever Ltd
Priority to US13/516,818 priority Critical patent/US8815219B2/en
Priority to PCT/CN2009/001544 priority patent/WO2011075871A1/fr
Priority to GB1210493.1A priority patent/GB2488493B/en
Priority to GB1210493.1A priority patent/GB2488493A/en
Publication of WO2011075871A1 publication Critical patent/WO2011075871A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin

Definitions

  • the present invention is directed to a composition and method for imparting a sunless tan to skin. More particularly, the invention is directed to a composition and method that employ a sunless tanning agent as well as an adjuvant for the sunless tanning agent.
  • the composition employs a pyranone furanone, derivative thereof or mixtures thereof as an adjuvant and, when applied, unexpectedly results in the consumer having skin with a brownish/tan coloration within a consumer acceptable time. Surprisingly, the composition does not result in color body generation even when the sunless tanning agent and adjuvant are stored together in a monophase.
  • Sunless tanning agents are formulated into two types of cosmetic products. Of these, the most traditional is the self-tanning lotion. The imparted benefit is to achieve a skin coloration equivalent to that from basking in the sun. More recently, a second product category has arrived. Therein a sunless tanning agent in small amounts is added to a typical moisturizing lotion. A "glow or shine" is thereby imparted. Glow or shine is a major factor in the appearance of healthy looking skin.
  • DHA dihydroxyacetone
  • Maillard reactions are believed (see, e.g., Bobin et al., J. Soc. Cosmet. Chem. 35: 255 (1984)) to lead to formation of brown pigments in the skin, thereby giving it an appearance similar to that of a naturally obtained tan.
  • compositions and methods for imparting a sunless tan are storage stable.
  • This invention is directed to a composition and method that employ a sunless tanning agent as well as an adjuvant for the sunless tanning agent.
  • the composition employs a pyranone, furanone and/or a derivative thereof as an adjuvant and, when applied, unexpectedly results in the consumer having skin with a brownish/tan coloration within a consumer acceptable time.
  • such a composition does not result in color body generation even when the sunless tanning agent and adjuvant are stored together in a monophase. Additional Information
  • compositions and methods that yield excellent sunless tanning results whereby the composition and method employ a sunless tanning agent and a pyranone, furanone, derivative thereof or mixture as an adjuvant.
  • the present invention is directed to a composition
  • a composition comprising:
  • the present invention is directed to a method for generating a sunless tan comprising the step of applying to the skin the composition of the first aspect of this invention.
  • composition means obtaining the suntan look by applying a topical composition.
  • composition is meant to include a substance applied to a human body for imparting a sunless tan where the composition is for example, a leave- on skin lotion, cream or mouse, shampoo, hair conditioner, shower gel, toilet bar, body wash, shaving cream, body wax, depilatory, mascara, sunscreen product or the like.
  • a composition may also be put on body towelettes for application to the body.
  • the composition of this invention is a lotion or cream.
  • Consumer acceptable time means within about 3 to about 6 hours from application, and preferably, from about 1 to about 2 hours, and most preferably, from about 15 to about 30 minutes subsequent to application.
  • a composition not resulting in color body generation means being storage stable where storage stable is defined to mean having no color bodies after about one (1) month of storage at room temperature and when formulated as a
  • the sunless tanning agent suitable for use in this invention is only limited to the extent that it may be applied topically on humans to form pigmented components.
  • Such materials may be alpha-hydroxyaldelydes and ketones, glyceraldehyde, troxerutin and related alcohol aldehydes, various indoles, imidazoles and derivatives thereof.
  • Illustrative yet non-limiting examples of the sunless tanning agents that may be used in this invention include dihydroxyacetone, melanin, mahakanni (eclipta alba), methyl glyoxal, erythrulose, alloxan,
  • the sunless tanning agent used is dihydroxyacetone, erythrulose or a mixture thereof. In a most preferred embodiment, the sunless tanning agent is dihydroxyacetone.
  • the sunless tanning agent makes up from about 0.025 to about 35%, and preferably, from about 0.05 to about 15%, and most preferably, from about 0.5 to about 10% by weight of the composition, based on total weight of the composition and including all ranges subsumed therein.
  • the adjuvant i.e., pyranone, furanone and/or derivatives thereof
  • pyranone, furanone and/or derivatives thereof that may be used in this invention is limited only to the extent that the same may be used in a composition suitable for topical application to humans.
  • the adjuvant is represented by the formulae:
  • each R 1 is independently H, CI, OH, or
  • each A is independently R 2 X- or H with the proviso that one A is R 2 X-; each R 2 is independently H, or Ci-4 alkyl;
  • each X is independently NR 2 , 0, S or
  • each Y is independently 0, NH, Ci-C 6 alkyl substituted N or S; and each Z is independently or H with the proviso that one Z is H;
  • n is an integer from zero to 6
  • q is an integer form 1 to 3.
  • the sunless tanning adjuvant used in this invention is 3-hydroxy-6-methyl, 4-pyrone, often known commonly as Allomatol.
  • the adjuvant makes up from about 0.025 to about 35%, and preferably, from about 0.05 to about 15%, and most preferably, from about 0.5 to about 8% by weight of the composition, including all ranges subsumed therein. It is also within the scope of this invention to employ mixtures of adjuvant represented by formulae I and II. Such adjuvants may be obtained from fungi like Aspergillus oryzae or by art recognized techniques including those which are initiated with a Kojic acid precursor. An illustrative example of the Synthesis of Allomatol, for example, is described in Japanese patent 4036217.
  • compositions of the present invention will typically include a cosmetically acceptable carrier.
  • Water is the most preferred carrier. Amounts of water may range from about 1 to about 99%, and preferably, from about 5 to about 90%, and most preferably, from about 35 to about 80% and optimally from about 40 to about 75% by weight, based on total weight of the composition and including all ranges subsumed therein.
  • the compositions will be water and oil emulsions, most preferably, of the oil-in-water variety. Water-in-oil emulsions, and especially, those generally classified as water-in-oil and high internal phase emulsions are, however, an option.
  • Other cosmetically acceptable carriers may include mineral oils, silicone oils, synthetic or natural esters, fatty acids and alcohols. Amounts of these materials may range from about 0.1 to about 50%, and preferably, from about 0.1 to about 30%, and most preferably, from about 1 to about 20% by weight of the composition, including all ranges subsumed therein.
  • Silicone oils may be divided into the volatile and non-volatile variety.
  • volatile refers to those materials which have a measurable vapor pressure at ambient temperature.
  • Volatile silicone oils are preferably chosen from cyclic or linear polydimethylsiloxanes containing from about 3 to about 9, and preferably, from about 4 to about 5 silicon atoms.
  • Linear volatile silicone materials generally have viscosities less than about 5 centistokes at 25°C while cyclic materials typically have viscosities of less than about 10 centistokes.
  • Nonvolatile silicone oils useful as carrier material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • the essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethylsiloxanes (like dimethicone) with viscosities of from about 5 to about 100,000 centistokes at 25°C.
  • An often preferred silicone source is a cyclopentasiloxane and dimethiconol solution.
  • suitable esters are:
  • Ether-esters such as fatty acid esters of ethoxylated fatty alcohols
  • Polyhydric alcohol esters such as ethylene glycol mono- and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl monostearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxy- ethylene sorbitan fatty acid esters;
  • Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate;
  • Sterol esters of which soya sterol and cholesterol fatty acid esters are examples thereof.
  • Fatty acids having from 10 to 30 carbon atoms may be included in the compositions of this invention. Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
  • Emulsifiers may be present in the compositions of the present invention. Total concentration of the emulsifier may range from about 0.1 to about 40%, and preferably, from about 1 to about 20%, and most preferably, from about 1 to about 5% by weight of the composition, including all ranges subsumed therein.
  • the emulsifier may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives.
  • Particularly preferred nonionic actives are those with a Cio- C 2 o fatty alcohol or acid hydrophobe condensed with from about 2 to about 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C2-C10 alkyi phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and di- fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- Cs- C 2 o fatty acids; and polyoxyethylene sorbitan as well as combinations thereof.
  • Alkyi polyglycosides and saccharide fatty amides are also suitable nonionic emulsifiers.
  • Preferred anionic emulsifiers include soap, alkyi ether sulfate and sulfonates, alkyi sulfates and sulfonates, alkylbenzene sulfonates, alkyi and dialkyi sulfosuccinates, C 8 -C2o acyl isethionates, Cs-C 2 o alkyi ether phosphates,
  • alkylethercarboxylates and combinations thereof.
  • Cationic emulsifiers that may be used include, for example,
  • Useful amphoteric emulsifiers include cocoamidopropyl betaine, C12-C20 trialkyi betaines, sodium lauroamphoacetate, and sodium laurodiamphoacetate or a mixture thereof.
  • emulsifiers include glyceryl stearate, glycol stearate, stearamide AMP, PEG-100 stearate, cetyl alcohol as well as
  • emulsifying/thickening additives like hydroxyethylacrylate/sodium
  • compositions comprising the sunless tanning agent and adjuvant of this invention to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives for compositions of this invention are alkyl esters of
  • preservatives are iodopropynyl butyl carbamate, phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol.
  • the preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion.
  • Preservatives are preferably employed in amounts ranging from about 0.01% to about 2% by weight of the composition, including all ranges subsumed therein.
  • Thickening agents may be included in compositions of the present invention. Particularly useful are the polysaccharides. Examples include starches, natural/synthetic gums and cellulosics. Representative of the starches are chemically modified starches such as sodium hydroxypropyl starch phosphate and aluminum starch octenylsuccinate. Suitable gums include xanthan, sclerotium, pectin, karaya, arabic, agar, guar, carrageenan, alginate and combinations thereof. Suitable cellulosics include hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethylcellulose and sodium carboxy methylcellulose. Synthetic polymers are yet another class of effective thickening agent.
  • This category includes crosslinked polyacrylates such as the Carbomers, polyacrylamides such as Sepigel® 305 and taurate copolymers such as Simulgel EG® and Aristoflex® AVC, the copolymers being identified by respective INCI nomenclature as Sodium Acrylate/Sodium Acryloyldimethyl Taurate and Acryloyl Dimethyltaurate/Vinyl Pyrrolidone Copolymer.
  • Amounts of the thickener may range from about 0.001 to about 5%, and preferably, from about 0.1 to about 2%, and most preferably, from about 0.2 to about 0.5% by weight of the composition including all ranges subsumed therein.
  • Fragrances, fixatives and abrasives may optionally be included in compositions of the present invention.
  • Each of these substances may range from about 0.05 to about 5%, preferably between 0.1 and 3% by weight.
  • cationic ammonium compounds may optionally be used in the compositions of this invention.
  • Such compounds include salts of hydroxypropyltri (C1-C3 alkyl) ammonium mono-substituted- saccharide, salts of hydroxypropyltri (C1-C3 alkyl) ammonium mono-substituted polyols, dihydroxypropyltri (C1-C3 alkyl) ammonium salts, dihydroxypropyldi (Cr C3 alkyl) mono(hydroxyethyl) ammonium salts, guar hydroxypropyl trimonium salts, 2,3-dihydroxypropyl tri(CrC 3 alkyl or hydroxalkyl) ammonium salts or mixtures thereof.
  • the cationic ammonium compound employed in this invention is the quaternary ammonium compound 1,2-dihydroxypropyltrimonium chloride. If used, such compounds typically make up from about 0.01 to about 30%, and preferably, from about 0.1 to about 15% by weight of the composition.
  • moisturizing agents such as substituted ureas like hydroxymethyl urea, hydroxyethyl urea, hydroxypropyl urea; bis(hydroxymethyl) urea; bis(hydroxyethyl) urea; bis(hydroxypropyl) urea; N,N'-dihydroxymethyl urea; ⁇ , ⁇ '-di-hydroxyethyl urea; N,N'-di-hydroxypropyl urea; N,N,N'-tri- hydroxyethyl urea; tetra(hydroxymethyl) urea; tetra(hydroxyethyl) urea;
  • hydroxypropyl appears, the meaning is generic for either 3-hydroxy-n-propyl, 2-hydroxy-n-propyl, 3- hydroxy-i-propyl or 2-hydroxy-i-propyl radicals. Most preferred is hydroxyethyl urea. The latter is available as a 50% aqueous liquid from the National Starch & Chemical Division of ICI under the trademark Hydrovance.
  • Amounts of substituted urea, when used, in the composition of this invention range from about 0.01 to about 20%, and preferably, from about 0.5 to about 15%, and most preferably,' from about 2 to about 10% based on total weight of the composition and including all ranges subsumed therein.
  • cationic ammonium compound and substituted urea in a most especially preferred embodiment at least from about 0.01 to about 25%, and preferably, from about 0.2 to about 20%, and most preferably, from about 1 to about 15% humectant, like glycerine, is used, based on total weight of the composition and including all ranges subsumed therein.
  • humectants may be employed in the present invention. These are generally polyhydric alcohol-type materials. Typical polyhydric alcohols include glycerol (i.e., glycerine or glycerin), propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. Most preferred is glycerin, propylene glycol or a mixture thereof. The amount of humectant employed may range anywhere from 0.5 to 50%,
  • composition preferably between 1 and 15% by weight of the composition.
  • compositions of the present invention may include vitamins.
  • Illustrative vitamins are Vitamin A (retinol), Vitamin B 2 , Vitamin B3 (niacinamide), Vitamin B 6 , Vitamin C, Vitamin E, Folic Acid and Biotin.
  • Derivatives of the vitamins may also be employed.
  • Vitamin C derivatives include ascorbyl
  • Vitamin E includes tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed. Total amount of vitamins when present in compositions according to the present invention may range from 0.001 to 10%, preferably from 0.01% to 1%,
  • Desquamation promoters may be present.
  • Illustrative are the alpha- hydroxycarboxylic acids and beta-hydroxycarboxylic acids.
  • the term "acid” is meant to include not only the free acid but also salts and C C 3 o alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone structures.
  • Representative acids are glycolic, lactic and malic acids.
  • Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from about 0.01 to about 15% by weight of the end use composition.
  • compositions of this invention may optionally be included in compositions of this invention.
  • the extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic.
  • Water and ⁇ ethanol are the preferred extract solvents.
  • Illustrative extracts include those from green tea, yarrow, chamomile, licorice, aloe vera, grape seed, citrus unshui, willow bark, sage, thyme and rosemary.
  • Also optionally suitable for use include materials like lipoic acid,
  • retinoxytrimethylsilane available from Clariant Corp. under the Silcare 1M-75 trademark
  • DHEA dehydroepiandrosterone
  • Ceramides (including Ceramide 1, Ceramide 3, Ceramide 3B and Ceramide 6) as well as pseudoceramides may also be useful. Amounts of these materials may range from about 0.000001 to about 10%, preferably from about 0.0001 to about 1% by weight of the composition.
  • the pH of the composition of this invention is from about 3 to about 4.75, and preferably, from about 3.25 to about 4, and most preferably, from about 3.25 to about 3.75, including all ranges subsumed therein.
  • Colorants, opacifiers, chelators (like tetrasodium EDTA) and abrasives may also be included in the compositions of the present invention. Each of these substances may range from about 0.05 to about 5%, preferably between 0.1 and 3% by weight of the composition.
  • the composition of the present invention comprises less than about 5%, and preferably, from 0.01 to 4% glycine, and most preferably, no glycine.
  • Packaging is often dependent upon the type of personal care end- use. For instance, leave-on skin lotions and creams, shampoos, conditioners and shower gels generally employ plastic containers with an opening at a dispensing end covered by a closure. Typical closures are screw-caps, non-aerosol pumps and flip-top hinged lids. Packaging for antiperspirants, deodorants and depilatories may involve a container with a roll-on ball on a dispensing end. Alternatively these types of personal care products may be delivered in a stick composition formulation in a container with propel-repel mechanism where the stick moves on a platform towards a dispensing orifice.
  • Metallic cans pressurized by a propellant and having a spray nozzle serve as packaging for antiperspirants, shave creams and other personal care products.
  • Toilette bars may have packaging constituted by a cellulosic or plastic wrapper or within a cardboard box or even encompassed by a shrink wrap plastic film.
  • the composition of this invention may be divided so that a first portion may carry sunless tanning agent and a second portion may carry adjuvant.
  • each portion should be packaged separately from each other and not come into contact with each other until application to the body.
  • the packaging for dual compositions is known and commercially available.
  • the make up of the composition i.e., the combined portions is as described herein.
  • ingredients may be combined in no particular order. Typically the ingredients are combined and mixed under conditions of moderate shear and at ambient temperature with pressure being atmospheric conditions. In a most preferred embodiment, DHA and adjuvant are not added at a time when mixing and heating are desired.
  • DHA and adjuvant are not added at a time when mixing and heating are desired.
  • When applied by the consumer typically from about 1 to 5 mg, and preferably, from about 1 to 4 mg, and preferably, from about 1.5 to 2.5 mg per square centimeter of composition is applied to body surface (like skin) and including all ranges subsumed therein.
  • Kojic acid (2.6 g) was dissolved in distilled thionylchloride (10 mL). The resulting mixture was stirred for about one hour at room temperature. The formed yellow crystalline mass was filtered and washed with petroleum ether and water sequentially to yield a chlorinated Kojic acid derivative. Such derivative (1.6 g) was added to 5 mL of distilled water and the resulting mixture was heated to 50°C with stirring. Zinc dust (1.3 g) was added and followed by the addition of concentrated hydrochloric acid (3 mL) with vigorous stirring. The resulting reaction mixture was stirred for an additional three (3) hours at 70°C. Excess zinc was removed by hot filtration and the filtrate was extracted with dichloromethane.
  • compositions comprising Allomatol were made by mixing the following:
  • glycine was provided to mimic amino acid condition of skin.
  • compositions as described below were thoroughly mixed and stored for about 10 hours at 35°C and 55°C.
  • compositions comprising Kojic acid or Allomatol were made by mixing the following ingredients at room temperature. Mixing was achieved with moderate shear and the balance of the compositions made was water.
  • Samples 1 through 5 were shown to out perform the control by 93%, 130%, 203%, 256% and 193%, respectively, as determined by assessing the Samples with a spectrophotometer, wavelength 400 nm.
  • Samples 1-5 were shown to out perform the control by 16%, 22%, 35%, 38% and 19%, respectively, as determined by assessing the Samples with a
  • compositions were made by mixing the following ingredients at room temperatures. Mixing was achieved with moderate shear and the balance of the compositions made was water. All percents are by weight.
  • Samples were assessed (with a Spectrophotometer, 400 nm wavelength) fifteen (15) hours after mixing.
  • the results revealed Samples 2 through 5 out performed the control by 40%, 17%, 2%, 6%, respectively. No color body generation was observed when the adjuvant was mixed with glycine and no DHA.
  • Synthetic skin, VITRO-SKIN ® was purchased from IMS Inc. The same is conventionally known to mimic the surface properties of human skin.
  • i ⁇ _* values at 4, 22 and 51 hours, read left to right.

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Abstract

La présente invention concerne une composition et une méthode d'autobronzage de la peau. La composition et la méthode utilisent un agent autobronzant comme la dihydroxyacétone combiné à un adjuvant qui est une pyrannone, une furannone ou l'un de leurs mélanges.
PCT/CN2009/001544 2009-12-24 2009-12-24 Autobronzant avec pyrannones et furannones Ceased WO2011075871A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US13/516,818 US8815219B2 (en) 2009-12-24 2009-12-24 Sunless tanning with pyranones and furanones
PCT/CN2009/001544 WO2011075871A1 (fr) 2009-12-24 2009-12-24 Autobronzant avec pyrannones et furannones
GB1210493.1A GB2488493B (en) 2009-12-24 2009-12-24 Sunless tanning compositon comprising dihydroxyacetone and pyranones
GB1210493.1A GB2488493A (en) 2009-12-24 2009-12-24 Sunless tanning with pyranones and furanones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2009/001544 WO2011075871A1 (fr) 2009-12-24 2009-12-24 Autobronzant avec pyrannones et furannones

Publications (1)

Publication Number Publication Date
WO2011075871A1 true WO2011075871A1 (fr) 2011-06-30

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PCT/CN2009/001544 Ceased WO2011075871A1 (fr) 2009-12-24 2009-12-24 Autobronzant avec pyrannones et furannones

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US (1) US8815219B2 (fr)
GB (2) GB2488493B (fr)
WO (1) WO2011075871A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8398959B2 (en) 2010-12-06 2013-03-19 Conopco, Inc. Compositions and methods for imparting a sunless tan with functionalized adjuvants
US8815219B2 (en) 2009-12-24 2014-08-26 Conopco, Inc. Sunless tanning with pyranones and furanones
US8821839B2 (en) 2010-10-22 2014-09-02 Conopco, Inc. Compositions and methods for imparting a sunless tan with a vicinal diamine
US8961942B2 (en) 2011-12-13 2015-02-24 Conopco, Inc. Sunless tanning compositions with adjuvants comprising sulfur comprising moieties
US8974548B2 (en) 2011-09-26 2015-03-10 Conopco, Inc. Hair composition

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GB2488493A (en) 2012-08-29
GB201210493D0 (en) 2012-07-25

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